Carboxin (syn: Carboxine) is an anilide systemic broad-spectrum fungicide and seed protectant. It is active against fungi like bunts, smuts, wilt, and powdery mildew. Its metabolites include carboxine sulfoxide and oxycarboxin. It can be used in chromatography and analytical methods. The compound is used to study fungal biology and in development of strategies for crop protection. Carboxin is useful in agricultural research and development applications.
Carboxin is soluble in DMSO.
| Mechanism of Action | Carboxin inhibits sterol biosynthesis of sterols in fungal cell membranes, which leads to their disruption of structure and function. As a result, cellular contents leak out and fungal cells die. It binds to the cytochrome b protein in the mitochondria, interfering with the electron transport. This impairs the energy production of the fungal cells, so that their growth is inhibited. |
| Spectrum | Carboxin is active against fungi including Phycomycetes, Deuteromycetes, and Basidiomycetes and others. It is normally used as a seed treatment on rice, corn, wheat, barley, oats, cotton, vegetables, and turf grass. It is also used for seedling diseases (ie Rhizoctonia spp.) of barley, cotton, maize, oats, peanuts, rice, sorghum, and soybean. |
| Molecular Formula | C12H13NO2S |
| Plant Biology | Carboxin was tested for its effects on the activities of mitochondria from fungi. At low concentrations it noncompetitively inhibited mitochondrial succinate oxidation from the sensitive fungus Ustilago maydis. Carboxin is not approved as a plant protection reagent in the EU per EC No. 1107/2009. |
| References |
Frampton CS, Frampton ES, Thomson PA. Two polymorphic forms of the oxathiin systemic fungicide active carboxine. Acta Crystallogr E Crystallogr Commun. 2018 Nov 9;74(Pt 12):1741-1745. PMID 30574366 Keon JPR, White GA and Hargreaves JA (1991) Isolation, characterization and sequence of a gene conferring resistance to the systemic fungicide carboxin from the maize smut pathogen, Ustilago maydis . Curr. Genet .19:475–481 |